2-Ethoxyphenol → HCID 13320246, compound

HRID 1262605Notes

Reaction equation

HRID 1262605 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[O:13][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])[CH3:15]>Cl.C(Cl)Cl>[CH2:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C@@H:11]1[CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][C@H:10]1[OH:13])[CH3:15]

Participants

5

Reactant 2

HCID 667552-EthoxyphenolHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

Product 1

HCID 13320246HCID 13320246, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 45.5 g. (0.26 mole) of 1-benzyl-3,4-epoxypyrrolidine (60 g. of 76% epoxide), 48 g. (0.35 mole) of o-ethoxyphenol and 8 drops of concentrated hydrochloric acid was heated at 145° C. for 16 hr. The mixture was cooled, dissolved in methylene chloride and washed with dilute sodium hydroxide solution. The methylene chloride layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on 1 kg. of silica gel using 20% acetone in benzene as the eluent. Two recrystallizations from cyclohexane gave 8.0 g. (10%) of tan needles, m.p. 88.5°-90.0° C.

Workup

  1. additionA mixture of 45.5 g
  2. temperatureThe mixture was cooled
  3. washwashed with dilute sodium hydroxide solution
  4. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was chromatographed on 1 kg
  7. customTwo recrystallizations from cyclohexane
  8. customgave 8.0 g

Sources & evidence

ORD record
ord-0713ff4b80734787a03543e610b11b7d
Source dataset
uspto-grants-1984_06
Patent number
US04452809

Reaction notes

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